Improved Condensation of 2-pyridyllithium Intermediates with Aldehydes: Application for the Synthesis of 2-(polyhydroxyalkyl)pyridines

被引:4
作者
Comoy, Corinne [1 ]
Petrignet, Julien [1 ]
Banaszak, Estelle [1 ]
Chartoire, Anthony [1 ]
Fort, Yves [1 ]
机构
[1] Nancy Univ, CNRS, SRSMC, F-54506 Vandoeuvre Les Nancy, France
关键词
Regioselective lithiation; n-BuLi/LiDMAE] superbase; 2-pyridinyllithium; 2-(polyhydroxyalkyl)pyridines; LITHIATION; CONVERSION;
D O I
10.2174/157017809787003214
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The scope and the limitations of 3-chloro-2-pyridinyl lithium condensation to aldehydes were envisioned depending on metallation conditions or condensation time and temperatures. The procedure was applied to various aromatic, aliphatic or functionalized aldehydes to afford a new and efficient access to 2-(polyhydroxyalkyl) pyridines.
引用
收藏
页码:50 / 56
页数:7
相关论文
共 20 条
[1]   New and efficient RCM in pyridinic series:: synthesis of 2H-dihydropyrano- or 2,3H-dihydrooxepino[3,2-b]pyridines [J].
Banaszak, Estelle ;
Comoy, Corinne ;
Fort, Yves .
TETRAHEDRON LETTERS, 2006, 47 (35) :6235-6238
[2]   Synthesis of the novel 1,7,9-trioxadispiro(4.1.5.2]-tetradecane ring system present in the spirolides [J].
Caprio, V ;
Brimble, MA ;
Furkert, DP .
TETRAHEDRON, 2001, 57 (18) :4023-4034
[3]   A novel and general α-regioselective and highly enantioselective prenylation of aldehydes [J].
Cheng, HS ;
Loh, TP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (17) :4990-4991
[4]  
Choppin S, 2001, EUR J ORG CHEM, V2001, P603, DOI 10.1002/1099-0690(200102)2001:3<603::AID-EJOC603>3.0.CO
[5]  
2-2
[6]  
Clayden J., 2002, TETR ORG CH, V1st, P1
[7]   New efficient access to thieno[3,2-b]pyridine derivatives via regioselective lithiation of 3-methylthiopyridine [J].
Comoy, Corinne ;
Banaszak, Estelle ;
Fort, Yves .
TETRAHEDRON, 2006, 62 (25) :6036-6041
[8]   Asymmetric synthesis of 2-deoxy-2-fluoro-gamma-aldonolactones and their conversion to 2-deoxy-2-fluoropentoses [J].
Davis, FA ;
Qi, HY .
TETRAHEDRON LETTERS, 1996, 37 (25) :4345-4348
[9]   Nickel-catalysed synthesis of 3-chloroanilines and chloro aminopyridines via cross-coupling reactions of aryl and heteroaryl dichlorides with amines [J].
Desmarets, C ;
Schneider, R ;
Fort, Y .
TETRAHEDRON LETTERS, 2001, 42 (02) :247-250
[10]   READILY ACCESSIBLE 12-I-5 OXIDANT FOR THE CONVERSION OF PRIMARY AND SECONDARY ALCOHOLS TO ALDEHYDES AND KETONES [J].
DESS, DB ;
MARTIN, JC .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (22) :4155-4156